@article { ISI:000321231700008,
	title = {Synthesis and properties of 2 {\textquoteleft}-O-[R- and S-(2-amino-3-methoxy)propyl] (R-AMP and S-AMP) nucleic acids},
	journal = {Tetrahedron},
	volume = {69},
	number = {31},
	year = {2013},
	month = {AUG},
	pages = {6404-6408},
	publisher = {PERGAMON-ELSEVIER SCIENCE LTD},
	address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND},
	abstract = {<p>Substitution at 2{\textquoteright}-position by either amino- or methoxy-pendant groups of the antisense oligonucleotides (AONs) is known to enhance their therapeutic value. A simple modification is described here in which we introduce both these groups in the form of enantiospecific tethers at 2{\textquoteright}-position. Practical synthesis of modified nucleosides using natural L-serine, en route to R-AMP- and S-AMP-AONs is presented. Such tethered ONs formed stable DNA:RNA duplexes and the stability was found to be marginally better than the methoxyethyl/methoxypropyl-substituted MOE/MOP-AONs. The stereochemistry of the tether effectively differentiated the hydrolytic cleavage of AONs and the R-AMP-AON was three times more stable than the S-AMP-AONs after 4 h. In comparison, the MOE- or MOP-AONs were almost completely digested by SVPD after 1 h. (C) 2013 Elsevier Ltd. All rights reserved.</p>},
	keywords = {Antisense therapeutics, MOE-AONs, Positively charged ON analogues},
	issn = {0040-4020},
	doi = {10.1016/j.tet.2013.05.104},
	author = {Kotikam, Venubabu and Kumar, Vaijayanti A.}
}
